ethyl (11S,17R)-17-glycoloyl-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl carbonate -Drug Synthesis Database

【结构式】

【分子编号】24005

【品名】ethyl (11S,17R)-17-glycoloyl-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl carbonate

【CA登记号】

【分子式】C₂₄H₃₂O₇

【分子量】432.51388

【元素组成】C 66.65% H 7.46% O 25.89%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(IV)

The esterification of prednisolone (I) with ethyl orthocarbonate (II) by means of p-toluenesulfonic acid in dioxane gives prednisolone 17,21-(diethylorthocarbonate) (III), which is carefully hydrolyzed with acetic acid water yielding cyclic prednisolone 17-(ethyl carbonate) (IV). Finally, this compound is esterified with propionyl chloride or propionyl anhydride in pyridine or CH2Cl2-dimethylaminopyridine, respectively.

参考文献中间体

合成目标

【1】 Zhao, H.-W.; Li, X.-Y.; Ginkgolide A, B, and huperzine A inhibit nitric oxide production from rat C6 and human BT325 glioma cells. Acta Pharm Sin 1999, 20, 10, 941.
【2】 Prous, J.; Castaner, J.; Prednicarbate. Drugs Fut 1986, 11, 6, 460.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	13538	(8S,9S,10R,11S,13S,14S,17R)-17-Glycoloyl-11,17-dihydroxy-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one; Prednisolone	50-24-8	C₂₁H₂₈O₅	详情	详情
(II)	28711	1-(triethoxymethoxy)ethane	78-09-1	C₉H₂₀O₄	详情	详情
(III)	24004	2',2'-Diethoxy-11-beta-hydroxyspiro[androsta-1,4-diene-17,4'-[1,3]-dioxane]-3,5'-dione; 2',2'-Diethoxy-11-beta-hydroxyspiro[androsta-1,4-diene-17,4'-[1,3]-dioxane]-3,5'-dione		C₂₆H₃₆O₇	详情	详情
(IV)	24005	ethyl (11S,17R)-17-glycoloyl-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl carbonate		C₂₄H₃₂O₇	详情	详情

Extended Information